Byte of Prevention Blog

by Jay Reeves |

5 Questions to Ask Before Going Out on Your Own

Open signYou’re tired of searching for a job that might not even exist, you’re questioning why you even wanted to be a lawyer in the first place, when suddenly you have an epiphany.

You’ll start your own firm.

The more you think about it, the better it sounds. You’ll be your own boss. You can sleep in whenever you want to. You will be the architect of your own destiny.

Hold on. Better talk to your spouse, partner or significant other first. Ask how they feel about it. How they really, honest-to-goodness, deep-down feel. Because without their support and encouragement, your road to success will be steep and rocky indeed.

“Doing your own business is tough—way tougher than I could have ever imagined,” writes entrepreneur and blogger Ali Mese. “Your mind is constantly messed up with a million things and no other person, including your partner, really understands what is going on in there. If you are not single, make sure your partner understands that your mind will often be a thousand miles away. You should explain to your partner that this distance isn’t because of them. You’re wrapped up, perhaps too much, in your own thoughts.”

So there’s one important question – how does your spouse feel about the idea – you need to ask before you become an entrepreneur. Let’s look at some others.

Do You Really Want To Be An Entrepreneur?

An entrepreneur, according to Merriam-Webster, is “one who organizes and operates a business and is willing to take on greater than normal financial risks in order to do so.”

Right off the bat we see several qualities that are indispensable to the entrepreneurial spirit:

  • You are a good (or at least competent) organizer.
  • You like the idea of running a business.
  • You are a risk-taker.
  • You have some money to risk.

5 Essential Inquiries

If you meet the above criteria, Mese – who is not a lawyer but left a cushy corporate job to launch a startup – recommends probing further by asking the following questions:

  1. Do I have enough money? The number one reason small businesses fail is because they are under-capitalized. Business experts recommend having enough savings to last one to three years.
  2. Am I good at thinking outside of the box? It is said that to succeed in solo practice it takes four Cs: capital, courage and confidence – and you have to be a little crazy.
  3. Can I deal with social pressure? Friends and relatives – especially those who aren’t entrepreneurs themselves – might not understand what you’re doing. They may think opening your own practice means you couldn’t get a real job. Or they may be nosy and inquisitive. Do you have any clients yet? Are you making money? Learn to block out the static and keep moving forward.
  4. Can I do without sleep? “Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week.”
  5. What is my definition of success? If it is to make a ton of money very quickly, prepare for disappointment. If it is to experience the satisfaction of turning a dream into reality, then that’s another story.

As Mese puts it: if you don’t build your dream, someone will hire you to help build theirs.

Have you started your own firm? What advice would you give to someone who wants to do the same?

Source: Ali Mese, Life Hacker

Jay Reeves a/k/a The Risk Man has practiced in North Carolina and South Carolina. Formerly he was Legal Editor at Lawyers Weekly and Risk Manager at Lawyers Mutual. Contact him at

About the Author

Jay Reeves

Jay Reeves practiced law in North Carolina and South Carolina. He was Legal Editor at Lawyers Weekly and Risk Manager at Lawyers Mutual. He is the author of The Most Powerful Attorney in the World, a collection of short stories from a law life well-lived, which as the seasons pass becomes less about law and liability and more about loss, love, longing, laughter and life's lasting luminescence.

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